5-氯噻吩-2-硼酸频哪醇酯 | 635305-24-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-氯噻吩-2-硼酸频哪醇酯
• 中文别名: 5-氯噻吩-2-硼酸频那醇酯
• 英文名称: 5-chlorothiophene-2-boronic acid pinacol ester
• 英文别名: 2-(5-Chlorothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 635305-24-7
• 化学式: C₁₀H₁₄BClO₂S
• mdl: MFCD08063140
• 分子量: 244.55
• InChiKey: DDDRRTOIHWNUSI-UHFFFAOYSA-N

物化性质

• 沸点：
  315.3±27.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chlorothiophene-2-boronic acid pinacol ester
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Chlorothiophene-2-boronic acid pinacol ester
CAS number: 635305-24-7

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, under −20◦C.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H14BClO2S
Molecular weight: 244.5

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-氯噻吩-2-硼酸频哪醇酯 在 4,4'-联吡啶 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以0.061 g的产率得到5,5'-dichloro-2,2'-bithiophene
  参考文献：
  名称：

  经由CH硼化的芳烃立体控制CH / CH均偶联。

  摘要：

  描述了一种温和的一锅法方案，该方案通过顺序的Ir催化的CH硼酸酯化和Cu催化的芳烃均偶联合成对称的联芳基。所形成的联芳基的区域化学空间上受CH硼酸酯化步骤的控制。该方法还成功地扩展到了杂芳烃。通过这种方法获得的某些产品无法通过Ullmann或Suzuki耦合协议获得。最后，我们显示了一锅序列描述了CH硼化/ Cu催化的均偶联/ Pd催化的Suzuki偶联以获得π扩展的芳烃骨架。

  DOI：

  10.1039/c9ob00995g
• 作为产物：
  描述：

  噻吩-2-硼酸频哪醇酯 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以40%的产率得到5-氯噻吩-2-硼酸频哪醇酯
  参考文献：
  名称：

  用N-卤代琥珀酰亚胺对芳基硼酸酯进行无金属卤化

  摘要：

  无需添加金属试剂即可完成芳基频哪醇硼酸酯的有效溴化和氯化反应。用富电子的芳基硼酸酯或杂芳基硼酸酯在DMF或乙腈中有效地进行反应，得到单，二或三卤代芳基频哪醇硼酸酯。

  DOI：

  10.1016/j.tetlet.2014.06.003

文献信息

• [EN] SUBSTITUTED PYRAZOLO[4,3-b]PYRIDINES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS<br/>[FR] PYRAZOLO[4,3-B]PYRIDINES SUBSTITUÉES ET LEUR UTILISATION EN TANT QUE MODULATEURS DU RÉCEPTEUR GLUN2B
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2020249791A1

  公开（公告）日：2020-12-17

  Substituted pyrazolo[4,3-b]pyridines as GluN2B receptor ligands. Such compounds may be used in GluN2B receptor modulation and in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by GluN2B receptor activity.

  取代的吡唑[4,3-b]吡啶作为GluN2B受体配体。这些化合物可用于GluN2B受体调节以及用于治疗由GluN2B受体活性介导的疾病状态、疾病和疾病的制药组合物和方法。
• Crystal Engineering of Angular-Shaped Heteroarenes Based on Cyclopenta[<i>b</i>]thiopyran for Controlling the Charge Carrier Mobility
  作者：Yanjun Qiao、Longfei Yang、Jiangyu Zhu、Chuan Yan、Dongdong Chang、Ning Zhang、Gang Zhou、Yan Zhao、Xuefeng Lu、Yunqi Liu

  DOI：10.1021/jacs.1c04576

  日期：2021.7.28

  Cyclopenta[b]thiopyran, isomeric to benzo[b]thiophene while isoelectronic to azulene, is involved as a building block to construct soluble organic semiconductors for field-effect transistors. Two series of angular-shaped heteroarenes based on cyclopenta[b]thiopyran, that is, Cn-SS (n = 4, 6, 8, 10) with different linear alkyl groups and C8-SS-Clm (m = 2, 3, 4) with chlorides substituted at different

  环戊二烯[ b ] 噻喃与苯并[ b ] 噻吩同分异构体，而与芴烯等电子，可作为构建场效应晶体管的可溶性有机半导体的基石。基于环戊[ b ]噻喃的两个系列角形杂芳烃，即具有不同直链烷基的C n -SS ( n = 4, 6, 8, 10)和C 8 -SS-Cl m ( m= 2, 3, 4) 在不同位置被氯化物取代，已直接合成。获得的七个 S-杂芳烃表现出有趣且相似的光物理和电化学特性，例如近红外吸收和最高占据分子轨道的高能级。然而，具有相同π-共轭骨架的S-杂芳烃表现出完全不同的分子堆积结构，这被证明是电荷载流子迁移率的关键决定因素。一旦烷基侧长度的工程，在最高的空穴迁移率Ç Ñ -SS系列是为实现Ç 8 -SS（1.1厘米2 V -1小号-1) 具有中等烷基长度。在C 8 -SS上进一步掺入氯化物导致缩短的分子间 H…S 接触和面间距。最有趣的是，当含氯的氯仿和氯苯用作结晶溶剂时，由于
• Rh^III-Catalyzed C–H (Het)arylation/Vinylation of <i>N</i>-2,6-Difluoroaryl Acrylamides
  作者：Huai-Wei Wang、Yu-Han Qiao、Jia-Xue Wu、Qiu-Ping Wang、Meng-Xin Tian、Yong-Fei Li、Qing-Xia Yao、Da-Cheng Li、Jian-Min Dou、Yi Lu

  DOI：10.1021/acs.orglett.0c03688

  日期：2021.2.5

  RhIII-catalyzed sp2 C–H cross-coupling of acrylamides with organoboron reactants has been accomplished using a commercially available N-2,6-difluoroaryl acrylamide auxiliary. A broad range of aryl and vinyl boronates as well as a variety of heterocyclic boronates with strong coordinating ability can serve as the coupling partners. This transformation proceeds under moderate reaction conditions with excellent

  丙烯酰胺与有机硼反应物的Rh III催化的sp 2 C–H交叉偶联已使用市售的N -2,6-二氟芳基丙烯酰胺助剂完成。广泛的芳基和乙烯基硼酸酯以及各种具有强配位能力的杂环硼酸酯都可以用作偶联伙伴。该转化在中等反应条件下进行，具有优异的官能团耐受性和高区域选择性。
• Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters
  作者：Jacob W. Clary、Terry J. Rettenmaier、Rachel Snelling、Whitney Bryks、Jesse Banwell、W. Todd Wipke、Bakthan Singaram

  DOI：10.1021/jo201093u

  日期：2011.12.2

  addition of pentane to the reaction mixture. DFT calculations (Gaussian09) at the B3LYP/6-31G(d) level of theory show that disproportionation of HMgBr to MgH2 and MgBr2 is viable in the coordinating ethereal solvents. This reaction also can be carried out under Barbier conditions, where the neat PinBH is added to the flask prior to the in situ formation of Grignard reagent from the corresponding organic

  格氏试剂（脂族，芳族，杂芳族，乙烯基或烯丙基）与1当量的4,4,5,5-四甲基-1,3,2-二氧杂硼烷（pinacolborane，PinBH）在环境温度下在四氢呋喃（THF）中反应为提供相应的频哪醇硼酸酯。最初形成的二烷氧基烷基硼氢化物中间体可快速消除溴化氢化镁（HMgBr），并以非常好的收率提供硼酸酯产品。在将戊烷加入到反应混合物中之后，溴化氢溴化铵（HMgBr）歧化为氢化镁（MgH 2）和溴化镁（MgBr 2）的1：1混合物。在B3LYP / 6-31G（d）理论水平上的DFT计算（Gaussian09）显示，HMgBr歧化为MgH 2和MgBr 2在配位醚溶剂中是可行的。该反应也可以在Barbier条件下进行，其中在从相应的有机卤化物和镁金属原位形成格氏试剂之前，将纯净的PinBH加入到烧瓶中。在Barbier条件下合成萘酚硼酸酯不能从反应性卤化物（例如苄基和烯丙基卤化物）中产生W
• Design and Synthesis of Arylthiophene-2-Carbaldehydes via Suzuki-Miyaura Reactions and Their Biological Evaluation
  作者：Shaukat Ali、Nasir Rasool、Aman Ullah、Faiz-ul-Hassan Nasim、Asma Yaqoob、Muhammad Zubair、Umer Rashid、Muhammad Riaz

  DOI：10.3390/molecules181214711

  日期：——

  A series of various novel 4-arylthiophene-2-carbaldehyde compounds were synthesized in moderate to excellent yields via Suzuki-Miyaura cross-coupling with different arylboronic pinacol esters/acids. The synthesized products were screened for their antibacterial, haemolytic, antiurease, and nitric oxide (NO) scavenging capabilities and interestingly, almost all products turned out to have good activities. 3-(5-Formyl-thiophene-3-yl)-5-(trifloromethyl)benzonitrile (2d) revealed excellent antibacterial activity, showing an IC50 value of 29.7 µg/mL against Pseudomonas aeruginosa, compared to the standard drug streptomycin with an IC50 value 35.2 µg/mL and was also found to be the best NO scavenger, with an IC50 value of 45.6 µg/mL. Moreover, 4-(3-chloro-4-fluoro-phenyl)thiophene-2-carbaldehyde (2i) exhibited a superior haemolytic action and an outstanding urease inhibition, showing an IC50 value of 27.1 µg/mL.

  通过与不同芳基硼频哪醇酯/酸的 Suzuki-Miyaura 交叉偶联，以中等至优异的产率合成了一系列各种新型 4-芳基噻吩-2-甲醛化合物。对合成产品的抗菌、溶血、抗脲酶和一氧化氮（NO）清除能力进行了筛选，有趣的是，几乎所有产品都具有良好的活性。 3-(5-甲酰基-噻吩-3-基)-5-(三氟甲基)苯甲腈 (2d) 显示出优异的抗菌活性，与具有 IC50 的标准药物链霉素相比，对铜绿假单胞菌的 IC50 值为 29.7 µg/mL值 35.2 µg/mL，也被发现是最好的 NO 清除剂，IC50 值为 45.6 µg/mL。此外，4-(3-氯-4-氟-苯基)噻吩-2-甲醛(2i)表现出优异的溶血作用和出色的脲酶抑制作用，IC50值为27.1 µg/mL。